Azo dyes



Patented Feh. 1 3,1940 I v v I AZO moss I doseph W. Lang, Woodstown, N. 5., and 'Crayton K. Black, Wilmington, Del., assignors to'E. I. 1111 Pont de Nemonrs & Company, Wilmington, Del;,

'a corporation of Delaware j STATES" PATENT FF No -Drawing. Application nugust'i,1937, I Serial No. 157,542,.-

9Clairns. romeo-262') This invention relates to dyes-pigments, and of 3 parts of sodium hydroxide- 7.5 parts of, lakes made from2-chlor-4-amino-to1uene-5-sulsodium carbonate "were vadded and. the .mixture ionic acidandbeta-hydroxy naphthoic acid. I cooiedto 18 C. Coupling was. effected in, the

' fAIflpigment or a lake made, from 2-ch1or-4 usual manner by adding the diazo component to 5 amino-t'oluene-5-su1fonic acid diazotized and he 2 :3-ox y-naphth'oic acid. The dye precipitated coL pled-wo heta-hydroXy-naphthoic acid and out as formed and was finished by heating: to, I laked is known and has good propertiesbut it 65 C. andfiltering. I I lacks certain tinctorial and-fastness efiects 1 The isolated "soda salt was reslurried to 2300 Itis an object of this invention to. produce partsof (water at theboiL 25'parts of calcium J colors/of the type described which haveimproved chloridein' 250 parts Water were :added during 5" tinctorial properties and improved fastness to minutes, Boiling was con'tinuedifo-r 10 minutes light and other constructive influences which. after which th'epi'gme-nt was filtered, washed, and affect this and similarpiginents. a dried The objects of the invention are accomplished," The resulting, pigment is very dark," and I generally speaking, by coupling beta-hydroxy- .brightH infrnass-tone, andv yellow and .stronglin' 15- naphthoic acid with a mixture of diazotized shade in comparison with a color made from 2 chlor-4-amino-toluene S-sulfoiaid acid and a 100% 2-chlor-4}amino-to1uene-5-si11fonic acid diazotizabie primary aromatic amine, represented but otherwise identical;

bytheformula: Example H I -o I I Y I I 1' Using the same procedure; as forEXample.I I,

v i substitute 104 parts of 2-ch'lor-4 aminoetoluene I I I '5 sulf onic acid and'add 0.7 part of 6 ch1or-2- I amino-toluene-5-su1ionic acid instead of "1.1V S0311 I parts of G-chlor-2- amino-to1uene-4-sulfonicacid t, for the ohazotization, The, resulting pigment m X represemts least dr or I is very'dark and bright in .top tone, and strong in1 auliochrome substituent"thereror such asai and blue in shade when compared with the I a Q n-? ?m and carboxyl, pigment made from pure 2-chlor-4- amino-to1u-. and sulfonlc ac ds, whlchis added to the main .i I v v one 5 sulfonic acid. intermediate 1n predetermined quant1t1es.-It 1s 1 II I I our siirprising discovery that this addition prof I I I duces a pigment of greater depth, more covering In diazotizing accordingt pme mjf power darker mass n randy'of qualities equal Example I use 10.4: parts .of 2-ch1or-4-amino-Y 1; another essential respects to Products 9 the toluene-,S-sulfonic acid and 0.6'part of 4-amino P I I 1 I trjlueh-Z-sulfonic acid. Completethe-couplihg The following ,examplesillustrate but do not dq ki gin Example The resulting limit theinvention. In these examples the parts e characterized by I a very dark are by weight. q I mass tonelincreased' strength and, blueness of fi l vshade, whencomparedwith the pigment made in y parts of 2'. n-am -t 1un -5- H the same manner with 2-chlor-41-amino-toluene-' acid and 1.1 parts of 6-ch1ore2-amino-toluene 5-Sll1f011ic' acidv I I I i sulfonic acid were dissolved in '100 parts-hot The new 5 have a e p and bright 1118155 water by the addition of 2il5 parts sodium hytone;-they are strong, fast to light, and have ex- .m dro'xide. The solutionwas acidified with 5 parts ep ional pigmenting properties in gen r T ey 45,

- 100% hydrochloric acid and iced to'0 C. Diazohave excellent working properties in printing tization was efiected by the addition of 3.5 parts inks, paintsand rubber in particular, andin genof sodium nitrite. 1 I I I erai iii-other places where pigments are useful.

10 parts of 2:3-oxy naph'thoic acidwere dis- As many apparentlywidely differentembodi- I solved in 100 parts of hot water bylthe addition merits of this invention may be made without 50 departing from the spirit and scope thereof, it is to be understood that we do not limit ourselves to the specific embodiments thereof except as defined in the appended claims.

We claim:

1. A composition of matter containing the members:

O! OH (30 OH and SOaH 0H 0 O OH I I 01 OH:

in predetermined quantities and so related as to be incapable of mechanical separation.

2. A composition of matter containing the members:

( 11 s OH coon I SO 3H and 0113 OH coon in predetermined quantities and so related as to be incapable of mechanical separation.

3. A composition of matter containing the members:

01 on coon H;CN=N V I 10313 I and soln OH coon in predetermined quantities and so related as to be incapable of mechanical separation.

4. The process which comprises coupling about 10 parts of 2:3-hydroxy-naphthoic acid simultaneously to about 10.4: parts diazotized 2-chlor-4- amino-toluene-5-sulfonic acid and about .6 part diazotized 4-amino-toluene-2-su1fonic acid, and laking the product with a calcium salt.

5. The process which comprises reacting about 10.4 parts of diazotized Z-chlorl-amino-toluene- 5-sulfonic acid and about .7 part diazotized 6- chlor-2-amino-toluene-5-sulfonic acid with about 10 parts of 2:3-hydroxy-naphthoic acid, and laking the product with a calcium salt.

6. The process which comprises coupling about 10 parts diazotized 2-chlor-4-amino-toluene-5- sulfonic acid and about 1.1 parts diazotized 6- chlor-2-amino-toluenel-sulfonic acid to about 10 parts 2:3-hydroxy-naphthoic acid, and laking the product with a calcium salt.

7. A composition of matter containing members:

0H coon and 0H 0 0 OH in which X is at least one of a group consisting of hydrogen, alkyl, alkoxy, halogen, nitro, amino, and carboxylic and sulfonic acids. in predetermined quantities and so related as to be incapable of mechanical separation.

8. The process which comprises reacting a mix- I ture of diazotized 2-chlor-4-amino-toluene-5- sulfonic acid and a predetermined quantity of a diazotized amine having the formula:

I S 03H in which X is at least one of a group consisting of hydrogen, alkyl, alkoxy, halogen, nitro, amino, and carbcxylic and sulfonic acids, with 2:3-hydroxy-naphthoic acid.

JOSEPH W. LANG. CRAYTON K. BLACK.

CERTIFICATE OF CORRECTION. Patent No. 2,1 9,806. February 1 ,19b .o.

JOSEPH W. LANG, ET AL. v

It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 1, second colunin, line 8, Example 1, for "to 2500" read in 2500; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Office.

Signed and sealed this 19th day of March, A; D. l9h0.

Henry Van Arsdale (Seal) Acting Commissioner of Patents. 

